Walk the runway—or the plank?

In a “previous life” (which is how I like to refer to my college years), I used to dress up like a pirate. This wasn’t an everyday occurrence, but I confess that I frequented more pirate-themed parties than Charles Bukowski frequented happy hours. At the time I thought it was acceptable to wear Jolly Roger dresses and gold Mardi Gras beads as belts. Although the handy “detag” tool on Facebook has enabled me to keep such images to myself (I’m a professional now), such youthful indiscretions have made me Portland Monthly’s resident pirate crackerjack.

Naturally, I felt compelled to set sail to the 2009 Portland Pirate Festival in Cathedral Park on September 19–20, to see if buccaneer fashion had finally evolved from the oh-so-2003 Jack Sparrow approach to more unconventional looks.

“It’s less about being historically accurate,” Dress Like A Pirate founder, Shayna Vest tells me. “This year many are mixing eras. We’re seeing a lot of bustle skirts, mini riding hats, and ruffled bloomers—overall more of a Victorian feel.”

Avast! Ye best 2009 pirate trends:

Buxom Beauties: Thanks to such vendors as Damsel in this Dress, wenches on the Willamette were outfitted in the finest—and tightest—corsets made from textured jacquard upholstery fabric. These essential items are made to accentuate everything we love about saucy buccaneer babes: their hips, their waists, and their, um, cannons.

Michelle Thorstrom’s custom creations are constructed with fiberglass rods dipped in rubber to give adorned women that perfect hourglass figure. Although historically women flattened their chests in the 1600s, Thorstrom stands firm in her belief that if the decolletage option was available in the 17th century, ladies would have happily taken it. “Do you really want to look like a tree’s stump?” she asks.

Scurvy dogs: In today’s age, the more bling you have, the more important you are. Well before rapper Rick Ross had his own face constructed out of diamonds for a medallion, Captain Barbarossa (aka, Captain Red Beard) had his head garnished in feathers. The more embellished the hat, the higher your rank. Duck, peacock, and semiplume tufts graced the heads of self-proclaimed captains as they watched Jake Duncan Digeridoo & The Highland Rebels spectacle. “You want something colorful, but not over the top,” costume designer Nyssa Baugher says about men’s headwear. “Its goal is to be eye catching, to let those know around you what your rank is.”

The men of Cathedral Park took it one step further. With vibrant hues of crimson and indigo, the feathers placed in each man’s hat were far more exaggerated than that of any seagoing swashbuckler of yore.

But don’t dump the parrot and peg leg quite yet. Although many women at the Portland Pirate Festival took their looks outside the box more than the men, traditional pirate style trends were still upheld in timeless fashion. After all, one can’t help but swoon for women in peasant blouses and men in eyeliner.